How Entourage 2008 fares with Exchange

Entourage 2008 ( ) may be Exchange-compatible—indeed, that’s one of its big selling points—but it isn’t the Mac version of Outlook. The last Mac version of Outlook—Outlook 2001—was built by the Microsoft Exchange team, not by the Mac Business Unit; it didn’t work unless it was connected to an Exchange server.

Even with the improvements in the latest version of Exchange, Entourage 2008 still doesn’t have 100-percent feature parity with Outlook for Windows. However, without porting a large chunk of Windows to Mac OS X, it never will. Outlook does some things that just require Windows. (You could always run Outlook on your Mac under Boot Camp, Parallels Desktop, or VMware Fusion.)

Nor does Entourage 2008 fix the majority of complaints about Entourage 2004’s ( ) Exchange support. A number of features users have been clamoring for—including syncing tasks and notes, the ability to manage Exchange Server Rules and to import and export personal folder files (PSTs), better integration of Exchange categories, and Distribution List management—are still undone.

The most obvious user-level improvement in the Entourage-Exchange relationship is support for out of office messages (OOFs), so you can automatically reply to e-mail when you’re out of the office (or just really busy). An Out of Office Assistant enables you to turn these messages on and off, set start and end times for when you’re out of the office, and specify who’ll get an OOF reply. You can also turn on a Reply Once To Each Sender Outside My Company With option, which keeps you from mail-bombing mailing lists you subscribe to with OOF messages.

Otherwise, most of the improvements in Entourage 2008’s Exchange support are in the plumbing. For me, the important element is Entourage’s Kerberos integration, which allows Entourage to work with Active Directory’s Single Sign-on infrastructure. If your Mac is bound to Active Directory via Directory Services, you can log into the Exchange server when you log in to your Mac with your Active Directory username and password. With Entourage 2004, you had to log into Entourage separately, set your Exchange password manually in Entourage, and change it manually when you changed your Active Directory password. When you change your Active Directory password, Entourage 2008’s Exchange password changes, too. It’s not task syncing, but it’s something IT types have been wanting for some time now.

There are also improvements in Entourage calendaring, specifically meeting management, stale invites, and conflict notification. The Entourage team is also looking to take advantage of the new Web Services conduits in Exchange 2007. Web Services is the new, preferred connection method in Exchange 2007, and will be the eventual replacement for the MAPI and HTTP-DAV messaging interfaces in clients like Entourage and Outlook. Since Exchange 2007 moves responsibility for automatically accepting meetings tentatively and resource scheduling to the server, Entourage 2008 gets those for free via Web Services. Web Services are probably the best way for Entourage to add Exchange features; unfortunately, that means that anyone who uses Entourage with Exchange 2000 or 2003 might not be able to use them.

[John C. Welch has been an IT administrator for almost 20 years, figuring out how to integrate Macs into almost every network type out there. He’s been writing about Macs, IT, and related topics since 1999.]

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